Bromine → 7-Bromo-2,3-dihydro-1-benzofuran-5-carbaldehyde

HRID 15361

Reaktionsgleichung

Reaktionsgleichung von HRID 15361
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]=[O:11])=[CH:9][C:4]=2[CH2:3][CH2:2]1.C([O-])(=O)C.[Na+].[Br:17]Br>C(O)(=O)C.S([O-])([O-])(=O)=S.[Na+].[Na+]>[Br:17][C:6]1[C:5]2[O:1][CH2:2][CH2:3][C:4]=2[CH:9]=[C:8]([CH:10]=[O:11])[CH:7]=1

Komponenten

6

Edukt 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 7359012,3-Dihydrobenzofuran-5-carboxaldehyde

Produkt 1

HCID 185261827-Bromo-2,3-dihydro-1-benzofuran-5-carbaldehydeAusbeute 91,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 24477Sodium ThiosulfateLösungsmittel

Versuchsvorschrift

To a solution of 2,3-dihydro-1-benzofuran-5-carbaldehyde (1.0 g, 6.75 mmol) in glacial acetic acid (8 mL) was added sodium acetate (664 mg, 8.1 mmol) and bromine (0.7 ml, 13.5 mmol) at 10° C. slowly. The reaction was stirred for 2 hours at ambient temperature. The reaction was diluted with a saturated aqueous solution of sodium thiosulfate (10 mL), washed with a saturated aqueous solution of sodium bicarbonate, and then extracted with ethyl acetate. Organics were combined, dried over sodium sulfate and dried in vacuo to give the desired compound (1.4 g, 91%).

Aufarbeitung

  1. washwashed with a saturated aqueous solution of sodium bicarbonate
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-fe868f260ebc4113b4e544be8e2d8359
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732461B2

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